


When We're Ready

by ilithiyarys



Category: Chicago PD (TV), NCIS
Genre: F/M, Hailey Upton & Ellie Bishop as siblings, Upstead, and it leads to some cute marriage talk, effective emotional communicators!upstead, fluffy upstead, i just wanted hailey to be a big sister okay, jay and hailey's thing, mentions of Ellie Bishop, random au i had in my head, specifically to ellie, the thing - Freeform, they do the thing okay
Language: English
Status: Completed
Published: 2020-11-26
Updated: 2020-11-26
Packaged: 2021-03-09 18:40:16
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,262
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27720838
Author URL: https://archiveofourown.org/users/ilithiyarys/pseuds/ilithiyarys
Summary: hailey gets a phone call from her younger sister, ellie, after she’d been promoted to senior field agent & agent in charge for her team. naturally, hailey’s competitive nature comes out as frustration and jay wonders why. fluffy stuff.
Relationships: Jay Halstead & Hailey Upton, Jay Halstead/Hailey Upton
Comments: 1
Kudos: 40





	When We're Ready

**Author's Note:**

> very much au. i just wanted to write hailey as a big sis. specifically to ellie bishop. so alas, mentions of ellie bishop - she’s not directly involved, but if this goes well i may write a fuller story around hailey & ellie’s relationship!

“You never told me about your sister,” Jay said. He had that twinge of curiosity in his voice.

The blonde brushed it off. “Not much to tell. She was always little miss perfect in the family. Moved to DC, got a fancy NSA analyst job and now works for NCIS.”

“Is that jealousy I’m hearing?” He prompted, quirking a brow.

“More like annoyance,” she mumbled under her breath. Jay was surprised, she’d never really mentioned anything about a sister until today, no less possibly being jealous of her. “You are totally jealous,” he gently prodded. The blonde rolled her eyes.

“Jay, I’ve had my fair share of federal job offers. You know that. I don’t fit into that life or the way they operate,”

“But?”

“But, nothing.” She attempted to deflect what he was getting at. Of course, to no avail.

“Hailey,”

“Jay, there isn’t much to say. I have an annoying younger sibling. That’s it.”

“Fine. But if you end up losing your shit later on because you’ve been thinking about your sister all day, I better not be your punching bag,” He sternly cautioned. 

After being partners for years, they knew each other well enough not to let anything that was bothering them go unsaid. They’d established that the moment they started doing _their_ _thing_ \- that no matter how frustrated or annoyed they were, that they wouldn’t become each other’s punching bags. This had become especially important after they’d started dating.

“Okay fine,” she sighed. Jay was right, she needed to get this out and vent. 

“Listen, it’s not that I don’t love her. I’d do anything for her. I mean, she’s my little sister. We were the only girls in the family and the two youngest. We had to stick together because we were all we had. Our brothers went off and did great things, and it was just the two of us for a long time. But life for her... She just always seemed to be in favour. It was Ellie that would get the scholarships, it was Ellie getting the crazy job offers, opportunities. Everything would just come right to her feet. And I’m not saying she’s lazy and doesn’t work hard - I have absolutely no doubt in my mind that she’s earned everything that’s come her way. The only reason I get so annoyed is because I just feel like such a failure compared to her. Like everything is just rubbed in my face. She’s married to a great guy, just bought a beautiful house, not to mention a very steady, well-paying federal job. Ellie, my baby sister leading a team of agents, exposing national threats, catching terrorists, has all these achievements and accomplishments... She’s got it all, and I just feel like such an underachiever. Like what have I done in my life?”

She paused, and Jay continued to listen.

“You know, other than you, I’ve never been able to hold down a steady relationship. Before meeting you, I would’ve jumped at every opportunity I got because I didn’t have anyone I was doing life with. But being with you, even with all the opportunities I get, I have no desire to take them. You’re all I need. But some nights I lie awake, tormented by the _what ifs_ and what life could have looked like if I had taken _that_ FBI job, or _that_ private security firm opportunity or _that_ unit sergeant promotion. I love police work and I'm a cop through and through but some days I don’t know if this is what I really want...”

The blonde let out a subtle, shaky breath. “... And that scares me because this is all I’ve got and know how to do. I’m just tired of not being enough.”

The brunette kept listening. He didn’t realize that she’d been carrying around this burden - was she truly happy here?

“Jay, you know I want it all someday - to get married, have a house, kids. But I can’t imagine the thought of me or you not making it back home one day.”

She felt vulnerable. This conversation was now bordering on new territory.

After listening to everything Hailey had said, Jay managed to gather his thoughts and offered them to her. 

“Hailey... I think you’re overthinking. It’s wonderful that you’ve thought about the future. But if you get too caught up in that, it’ll rob you of the now. You are exactly who you were made to be and exactly where you need to be right now. You _are_ enough. And what we do... I mean, that’s always going to be the complicated thing about working in law enforcement. There’s never that promise or guarantee we’ll make it home at the end of the day - that’s the unfortunate reality of bad people being on the streets. But _when_ we get to put someone away, when we get criminals off the streets, it’s so rewarding. We get to make the city a little safer and people can rest, people can eat, people can breathe and people can sleep a little better knowing that _that_ pedophile, _that_ serial killer, _that_ stalker, _that_ gangbanger, _that_ rapist, _that_ shooter, _that_ bomber, is off the streets. We get to do that, and it’s what makes this line of work so worth it.”

She nodded, continuing to listen to him. For a man of few words, he carried so much wisdom.

“And listen, sure, your sister may seem like she’s living this perfect life, but that’s her life. Yours is your own. You have different experiences, you’ve gone through some things. You’ve experienced your own losses, but you’ve experienced some even better wins. Comparing yourself to someone else will never do you any good - it’ll just rob you of everything you’ve built and established now. And Hailey, honey, I think you’re doing so good. I am so proud of you. I don’t think you should worry or read into too much about where you are or aren’t at right now. That’s the beauty of the present, it’s a gift. You never know what it’ll hand to you. I mean, it gave me you,”

He gave her that signature, charming, boyish smile that just melted her. “You, Jay Halstead, have a way with words,”

Hailey’s eyes were red-rimmed now. He always knew how to get through her walls. They’d sat in silence for a few seconds before Jay reached for her hand.

“I’m also hoping you weren’t taking a dig at me for taking it slow with you... You know I want to marry you. Every night I dream about the day I’d finally get to call you my wife. I want to spend the rest of my life and days with you. I want it all too. But I want to respect what we’ve talked about - about it not being the right time right now. Unless that’s a conversation you want to revisit?”

Hailey shook her head, wiping the tears from her face. “No, not at all - that’s my bad. I should’ve phrased it better. Jay, I love you with every single ounce of my being and that will never change. You are everything to me and more, and I don’t wanna rush into things just because I’m having an existential crisis. We’ll do it when the time is right. You always have impeccable timing.”

“I love you,” he whispered, leaning in to kiss her. “I love you too. Thanks for this, Jay.”

“Of course. You’re my partner at work and at home. This is what we do. Now let’s go get our perp.”


End file.
